How was it possible that I did not discover this excellent TL for so long? Just spent the last two days reading though the entire thing, all I can say is thank you so much for writing this amazing, yet chilling TL, and I am glad that it is still currently on-going.
Not many maps of it in the Map Thread, if any. I think that is usually the best way for people to get attentoin in or their timelines, even if it acts as a bit of a spoiler. Still, the title for this timeline is rather subdued. Seems more like an actual book than a work of online fiction.
So I think he would be remember well, but his image will suffer a lot for being so friendly and trusting of Stalin, and USSR. Churchill in fact would be remember better as the man who saw the threat of the Soviet Union, Stalin, and Communism from the stater and ahead of FDR.
People may be a bit concerned about the public works programs of FDR, but they may forgive him to an extent. People calling themselves "Progressive" earlier in American history will be put under suspicion. Theodore Roosevelt would be given a pass, especially given his personal hostility to Russia and the Kaiser. Henry Wallace, though? His run for president as part of the Progressive Party (not sure if it has continuity from the Bull Moose one) might taint the word, while FDR gets the accolades for having booted him before he died. Might be suspicions emerging that FDR was being slowly poisoned, worked to death, whatever so that Wallace would get to be president and Stalin's useful idiot. They might tie it into how Stalin never went far for Big Three Conferences, people claiming he was trying to drain FDR further. And for the Casalbamnca conference between Churchill and Roosevelt, I believe there was problems with a naval vessel firing upon the President's ship twice. Conspiracies aho! Ahh, and various demagogues like Huey Long, Father Coughlin, etc will be painted as commies.
Ahhh, and anyone got a TVTropes account? Last time I checked this thread's page, it mentioned a guy being tried under law as against socialists because of national socialism, underscoring the second word. Or something. Pretty sure he was tried for Holocaust denial.